


First Time

by sometimesiwritespn



Series: Ageplay/Involuntary Regression [10]
Category: Supernatural
Genre: Additional Warnings Apply, Age Play, Age Play Caregiver Dean Winchester, Age Play Caregiver Sam Winchester, Comfort, Domestic Fluff, Embarrassed Reader, Embarrassment, Emotional Hurt, Emotional Hurt/Comfort, F/M, Fluff, Infantilism, Mild Hurt/Comfort, Non-Sexual Age Play, Non-Sexual Intimacy, Other Additional Tags to Be Added, Reader is all blushy, Sam's adorable, Tooth-Rotting Fluff
Language: English
Status: Completed
Published: 2018-09-06
Updated: 2018-09-06
Packaged: 2019-07-07 14:38:17
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 4,605
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15910281
Author URL: https://archiveofourown.org/users/sometimesiwritespn/pseuds/sometimesiwritespn
Summary: (Y/N) and Sam have been dating a while and she regresses for the first time -- but only because Sam convinces her to.





	First Time

**Author's Note:**

> Okaaay, so! This was requested by Happy and Healthy, asking for basically where the reader is stressed and Sam coaxes her into regressing, but he's super cute and adoring and makes her all blushy. I pretty much blushed while writing this just thinking about it, so I hope this is okay! She's embarrassed and scared Sam & Dean will think she's stupid, so they convince her otherwise. 
> 
> Also, literally the whole thing is Sam trying to convince her into it, I don't really do much with him actually taking care of her while regressed. So I mean, part 2 maybe? But you guys have to let me know if you actually want a part 2. Comment & subscribe if you do! 
> 
> Comments & kudos mean the world, I hope I did the request justice, thank you for thinking of me to write it! <3

(Y/N) was a little, and she hated admitting it. Even to this day, she hadn’t actually admitted it out loud. She was embarrassed by it, afraid that she would be judged by everyone who found out. The less people she told, the better. So, she told no one. 

Then, her entire life changed in the form of one hazel eyed man named Sam Winchester. He’d saved her from a Wendigo, but everyone else she knew had been killed by it. She had no one else left, so he and Dean decided to take her in until she could get back on her feet. The rest? Well, the rest was history. 

(Y/N) never learned to hunt. She had no interest in it. Sometimes she would help with the research, but she was not the type of person to throw herself into danger. Not after that Wendigo killed her entire family. She hated that even Sam and Dean went out and did it, but she knew that was what they were made for. That was one of the reasons she loved them so much. 

Sam, having gone to college, had been exposed to many things. Even though it was at Stanford, there were still a lot of things that happened behind the scenes no one talked about. One night, Sam had found himself being dragged into a kink party (they’d just told him it was a party, and he had no reason to suspect otherwise), and he’d found out a lot of things he didn’t know before. One of them was the kink of ageplay. The whole thing weirded him out a little bit, until someone’s ‘daddy’ took pity on him and started to explain that yes, they did it as a kink, but there were many people out there that didn’t do it for a kink.

This man explained it was a way for ‘littles’ to feel safe. The real world just got too overwhelming for them, and they needed a way to let go, and this was a safe way to do it, as long as they had someone to take care of them. They loved pajamas, and pacifiers, and bottles/sippy cups, sometimes diapers, coloring books, stuffed animals, and most of all, snuggles. They just needed to take a break from the real world for a little while. 

The guy also explained that this wasn’t a widely accepted thing, and in fact, had been shown on a TV show called ‘My Strange Addiction’ and received a lot of backlash. Because of it, most littles were very hesitant as to who they would tell, if they told anyone at all. “My little girl refused to tell anybody. Ever.” He had said, which had Sam intrigued. 

“If she refused to ever tell anybody, how did you find out she was a little?” He asked, which started an entirely different part of the conversation. The man talked about the little subtle signs that some littles had. Sucking their thumb when they were tired or thought no one was paying attention to them, getting upset easily, starting to talk in a ‘littler’ voice, wanting to be snuggled up in pajamas, and even some more not-subtle things, like looking longingly at some of the baby stuff while being at the store, or researching it online. 

That had been fifteen or so years ago now, but Sam had never forgotten it. It’d gotten pushed to the back of his mind throughout the years, since he never had any reason to think of it, but every so often when he was in the store and saw the baby things, he thought back to that conversation. He thought rather fondly of it, how it might be pretty cute to have a little. As long as it wasn’t sexual when they were in their little space – he shuddered at the thought of it. Props to those who could do it, and he wasn’t judging; it’s just something he wouldn’t be able to do himself. 

Bringing them back to the present day, that conversation was how Sam realized (Y/N) was a little without her ever saying anything about it. He’d caught her about to suck her thumb quite a few times, and actually sucking her thumb once. He noticed she had onesies that she would wear every so often, and on those nights, she would be even more clingy to Sam than she already was as his girlfriend. 

He’d talked to Dean about it late one night, just letting him know what he was seeing. Dean was okay with it and would gladly help take care of her if that was what she wanted. Sam made sure he didn’t say anything to her about it, though, since he hadn’t even spoken to her about it. He didn’t want her to feel like she was being ambushed. 

Then, one night he’d sat (Y/N) down to talk about it. “You’re a little, aren’t you?” Sam had asked softly, knowing by how her eyes widened and her cheeks heated up immediately that he was spot on. He also knew this was one of those situations like with the guy he’d talked about, where she would never want to admit it no matter what. “It’s okay.” Sam said softly. “I’ve known what they are for a long time now. I’ve never taken care of one, but I’ve thought it was an adorable concept since I found out about it. You just let me know if you ever want to do anything, okay?” 

(Y/N) hadn’t even answered, just changing the topic of the conversation to what they were going to have for dinner that night. But the entire night, (Y/N) hadn’t stopped sneaking little glances at Sam, and he saw them. He could see the wonder in her eyes. Wondering how he realized she was a little, if he really was okay with it, if there was possibly a chance of her ever being to realize her dream as a little. The entire night, Sam had just treated her how he always did, wanting her to realize things weren’t going to change just because of what he’d found out. 

That conversation had been months ago now. Sam had almost forgotten they’d even had the conversation, since (Y/N) had never once acted like she wanted to do it. In fact, it seemed like she’d hardened herself against it ever since she realized Sam knew. He never caught her almost sucking her thumb anymore. He never caught her looking at things longingly in the store. He never caught her glancing around before looking something up on her phone that she didn’t want anyone to see. Life just went on as normal. 

(Y/N) had taken on a small job working for an online writing blog. It was an easy way to make some extra money and still be able to use a fake name. Kevin had managed to set it up, so no one would be able to look up any IP address from the blog she was using, and eventually she had settled into it. It was something that made her happy, because she felt like she was finally contributing something to what Sam and Dean were doing. She was at least helping provide them with a little bit of money, even though it wasn’t much. 

Sometimes, though, the writing was stressful. The deadlines were too soon for too much. The prompts were too hard or triggering for what she had gone through with the Wendigo. Sometimes it was just a simple prompt that would send her spiraling, but it wouldn’t be simple to her, because it reminded her of her brother, or her father or mother. Most of the time she loved the writing, but just like every job, there were good days and bad days.

Slamming the laptop shut, (Y/N) scrubbed her eyes with her hands while she furiously tried not to cry. The prompt this week had been a murder story. She’d been hesitant already, but when she actually started to write it, that was when everything had come crashing down.

Right when (Y/N) got the prompt, Sam knew this was likely what was going to break her down the most. “I think it might be this week.” Sam said quietly to Dean, who then asked him what the hell he was talking about. “I’m going to try to convince her to regress. With that prompt she just got for work, I think she’s going to be having a really hard week. I’m hoping I can get her to regress toward the middle of the week and it will help with her stress levels for the rest of the week, so she can get the prompt done.” Dean had then said he would help out with her if Sam needed any help, which Sam thanked him for, even though he had a feeling he wouldn’t need Dean’s help. 

Sam had already bought a bunch of things for her being little, in case it ever happened voluntarily, or in case he ever had to coax her into it. Pacifiers, bottles, sippy cups, diapers, supplies for diaper changes, a couple cute onesies, and more. He’d also been making sure they kept fresh milk in the fridge all the time in case she happened to regress, and she wanted a bottle. (Y/N) had been a little weirded out at first when Sam started to do that, but he’d just told her it was because he was having cereal for breakfast every morning, and she’d let it go. 

“I fucking hate this prompt.” (Y/N) muttered quietly, taking a deep breath before looking up at Sam. “Who the fuck thinks it’s a good idea to have a murder prompt? Don’t they know that people have relatives who have been murdered?” 

Sam gives her a sad smile, opening his arms to her. “How about you give up on that for the night, gorgeous?” He asks, wrapping his arms tightly around her when she huddles into his chest. Sam leans his head down, so he can kiss the top of her head, squeezing her reassuringly. They both knew it was a normal sort of prompt – tons of writers wrote about that; however, it didn’t make her writing about it any easier. “I think getting in bed would do you a world of good.” 

(Y/N) nods her head in response, her face still hidden in her boyfriend’s chest. She hated burdening him with this all the time, but she couldn’t help it. It really hadn’t been that long ago – less than a year since her entire family had died. She felt like it was still acceptable for her to be grieving. Sam also had told her she could grieve for as long as she needed to – and he would never judge her for how she grieved or for how long she grieved. “I’m sorry.” She whispers, voice so quiet it takes Sam a second to realize what she’d said.

“Hey, no. Don’t be sorry.” Sam says gently, smiling down at her. “You know you can come to me whenever you’re feeling sad. I never want you to be sorry about it.” He squeezes her reassuringly before pulling away, so he can grab her hand. 

“Hey. You don’t think you’re going to bed without saying good night to me first, do ya, kiddo?” (Y/N) turned when she heard Dean’s voice, seeing him with his arms outstretched to her. He wasn’t normally a super affectionate person, but when he knew she was upset like this, he always got super affectionate in hopes it would help her at least a little bit.

A smile forms on her face as she sees Dean looking rejected, moving toward him and hugging him tightly. He pulled her into his chest, rubbing her back briefly for a moment. “I love you.” (Y/N) whispers, smiling softly again when Dean lets go of her from the hug.

“I love you, too, kiddo.” Dean says, ruffling her hair. (Y/N) rolls her eyes playfully when he ruffles her hair, but just goes back to Sam. Ever since she’d come to live with them in the bunker, Dean had constantly been calling her kiddo – even before they knew anything about her regressions. Now it just happened to be more fitting, but (Y/N) still wasn’t suspicious of anything.

Sam’s hand was outstretched to her as (Y/N) returned to him, so she held out her hand to grab his. Their fingers lock together how they always do, which already has (Y/N) starting to relax a little bit, but she’s still stressed out to the max, and Sam can tell. He knows this is the perfect night to try to coax her into relaxing enough to regress. Sam knew she found it embarrassing but hoped that since he was trying to convince her to do it, instead of her asking to do it, that she would be okay with it. 

Once they got into the bedroom and Sam had closed the door, it was like he completely turned a different person. Of course, he was sweet with (Y/N) no matter what, but once his brother was no longer in the picture, he became even more sweet and mushy, which always got (Y/N) blushing. “Alright, baby.” He coos, and (Y/N) feels her cheeks heating up before he even says anything else. “How about we get you into some jammies, huh?” 

(Y/N) looks down shyly, but there’s a small smile on her face that’s only growing. Sam moves to the closet, so she looks to see what he’s doing, blushing even more when he pulls out one of the new onesies he’d bought her that she hadn’t even seen. It looked extremely fluffy, and she was really excited about it, even though she was trying to act like it wasn’t a big deal. “When did you get that?” She asks, and Sam doesn’t miss how her eyes widen in wonder and her voice starts to go just a tiny bit little. 

Sam grins. “I got it a few days ago when I went to the store. I wasn’t planning on getting anything like this, but when I was wandering near the pajamas I saw they were on sale, so I grabbed a couple. This one’s a tiger, do you like it? It’s ferocious, just like my baby.” 

Now (Y/N) feels like her cheeks are on fire, and she has a slight inkling that she might know what Sam is doing, but she’s ignoring it for now. She wants to see where this is going to go. And slowly, piece by piece, Sam is knocking down her resolve to refuse to be little. How could she continue to refuse when he’s starting to pull out things she’s wanted for most of her life, and has just never had the courage to ask for? 

“I love it.” (Y/N) answers shyly, looking down at the floor when Sam drops the onesie on the bed and comes up so he’s standing right in front of her. Even though this is her Sam, the one she’s most comfortable around, she can’t help but be shy when he treats her like this. He treats her like a princess, something she’d always dreamed of, but had always thought she’d never have. She’d been treated badly in many of her past relationships and had always figured there was never anything else out there for her except for being treated like shit.

“Let’s get you out of these rough and yucky clothes, huh?” Sam coos to her, and now (Y/N) knows that she was right – he was trying to get her to regress. But she was starting to harden herself against it again, because if he had simply gotten her new footy pajamas, she wouldn’t be able to regress. She wouldn’t have most of the things she needed in order to regress. Little did she know how prepared Sam truly was. “Alright, buttercup. Arms up.” 

Sam does as she says, and he helps pull her shirt from her body, doing the same with her bra. He then unbuttons and unzips her jeans, kissing her tummy when he kneels down to do so, and (Y/N) feels like her cheeks are going to be lit on fire if she blushes anymore than she was right then. She knew she must look like a tomato. Great, real attractive.

Once her jeans and socks are off, Sam gestures for her to sit on the bed. He grabs the onesie in his hands before suddenly gasping dramatically and placing it back down on the bed. “You know what? I forgot something.” He turns around and almost disappears into the closet, leaning over so far in because he’s rummaging for something. (Y/N) is watching with interest, wondering what on earth he could have forgotten that was so far back in the closet. “How about this, sweet pea?” 

(Y/N) practically gasps when Sam turns around and he’s holding a diaper in his hands. She quickly clamps her teeth down on her lip to stop her from making a sound, her hands coming up to her cheeks to hide how inflamed they are just from the suggestion. “Sam…” She says quietly, her voice almost a whine – and yes, another pitch into a little voice. 

“Hey, hey. No whining, gorgeous.” Sam says softly, leaning forward so he can place a gentle kiss to her lips – more than likely the last one until she decides she doesn’t want to be little anymore. “I bought ‘em specifically for you, and for this. It’s okay, I promise. I can see that look in your eye, baby girl. And I just think you would look so darn cute with a little padded bottom.” He grins, knowing that the words would just make her even more shy, and to no surprise, they did. 

“Dean’s gonna think I’m stupid.” (Y/N) mumbles quietly, her eyes cast downward. “What if you think I’m stupid after we actually start doing it?” She couldn’t imagine Sam being forced to take care of her while thinking she was crazy – and then likely breaking up with her once she decided to be big again. Or if Sam thought she was stupid and dumped her on Dean, who also thought she was stupid. She was just going to be far too much of a burden. 

Sam smiles softly, gently poking her nose. “I’ve already talked to Dean about it, little one.” He says softly. “And he says he’s more than willing to help take care of you if I need it or if you want it. I promise, I’m not going to think you’re stupid. Like I’ve said before, I’ve known about it for a long time now, and I always thought it would be cute to have a little of my own. Now I just actually get to have one.” He gently places his thumb and index finger on her nose, so he can squeeze it, before leaning forward to kiss her nose. “I’ll take care of you. Whatever you need, I got it. If you want to use your diaper, use it. If you want to snuggle with Dean, or have Dean do something for you, we got it. You can be little for as long as you like.” 

(Y/N) couldn’t believe Sam had been planning that for this long, had even had conversations with Dean about it, and she had never heard anything about it. She had no idea he’d bought stuff and had been planning on convincing her to let go. Even still, she was still having a hard time letting go. “I don’t know…” 

Sam gives a soft smile. He’d thought he’d mostly broken her down, but obviously she still had some reservations about the whole thing. “Come on, little one.” He coos, still holding the diaper out to her. “You know you want it… and I think you’d be cute as a button in it, so what do you say we give it a try?” 

Even though her cheeks are inflamed once more, (Y/N) slowly nods her head. Sam silently praises himself in triumph that he’d finally gotten her to give in. “Alright, baby girl. Lay back.” He says softly. Once she did so, Sam got her to lift her hips, so he could get her panties off, and then proceeded to change her into a diaper. The entire time he was doing so, she was looking away, obviously embarrassed. 

What he didn’t expect, though, was that when he finally finished and got her all dressed up in the onesie, that she would have tears in her eyes. “Ohh, hey, baby… what’s wrong?” Sam asks as he takes her hand to pull her into a sitting position. “It’s okay, sweetheart. Nothing’s wrong. Everything is okay.” 

“E-Em-Emb…” (Y/N) starts to say, but her lip is trembling, and her voice is quivering so much that she can’t even say it. She also can’t look Sam in the eye, afraid that when she looked at him, he would be teasing her about it. 

“You’re embarrassed?” Sam asks softly, gently using a finger under her chin to turn her head, so she’ll look at him. “Baby girl, there is absolutely no reason to be embarrassed. I think you’re as cute as a button. And you’re still my fierce little tiger, aren’t you? You’re Sammy’s fierce little tiger. And if you want, I can promise that you can stay in my room the entire time. I won’t take you out of here if that’s what you want.” He’d have to leave her for a few minutes at a time, so he could get her a bottle and other things if she wanted them, but she never had to leave the room, if her big worry was Dean seeing her. 

“Sammy’s fierce little tiger.” (Y/N) repeats quietly, looking down at the onesie with the tiger stripes on it, as well as some little dots of color here and there. She had to admit, it felt good being in the onesie and the diaper. She just hated to think that either one of them would judge her for it. “De think I’m stupid?” She asks, Sam smiling as she finally starts to let go enough that she’s using her little voice. 

Sam shakes his head. “Absolutely not. Dean will not think you’re stupid. What do you say we go out in the kitchen for a few minutes? I can make you a bottle and you can see Dean, so he can tell you himself that he doesn’t think you’re stupid.” He can see she’s hesitant about it, which he figured would be the case, but she was also thinking about it. “You know what? I forgot one more thing.” 

(Y/N)’s eyes widen from excitement and nerves when Sam mentions forgetting something else. Was it something else for her being little? More than likely, if he was talking about it in the same way he did as the diaper. She also had one other thing she really wanted, but she wasn’t going to ask for it. She refused.

“You ready for it?” Sam asks, after rummaging around in a little plastic bag for a few moments. He builds up the excitement for her until she practically can’t take it anymore, then finally holds out his hand. In it lays a small pacifier, a green one, with a puppy on it. 

(Y/N) can’t help the gasp she lets out now, and she quickly reaches her hand out for it. Sam can tell she’s finally slipping more into her little space, finally starting to accept it, and then she withdraws her hand. Sam quirks an eyebrow and asks her why she doesn’t want it anymore, but she then answers a second later, “Sammy put it in?” 

Sam’s heart melts when he realizes she took her hand away because she didn’t want to put it in her mouth herself, she wanted him to do it for her. “Of course, sweet girl.” He whispers, gently placing the pacifier in her mouth. “You want to go out to the kitchen for a few minutes? I’ll even carry you.” He says coaxingly, outstretching his arms to her.

(Y/N) stays silent for a moment while she debates it before slowly nodding. She needs to know if Dean thinks she’s stupid or not. She can’t just take Sam’s word for it – and she’d rather know now, before she slipped too far into little space. Before she wanted to do it so much that she couldn’t pull herself out of it. 

Sam scoops her up off the bed, smiling as he does so. He kisses her forehead, settling her on his hip while he carries her out to the kitchen. “Dean? You out here? Someone wants to see you.” He made sure to keep a different tone of voice than he normally did so Dean would realize that he had gotten (Y/N) to regress. 

Dean quickly picked up on what Sam was saying, getting up from where he was sitting on the couch and coming into the kitchen. He couldn’t help but to grin as soon as he saw them, seeing (Y/N) all dressed up in a onesie and curled up in Sam’s arms, even sucking on a pacifier. It was adorable. “Well hey, kiddo.” Dean says, smiling at her. He reaches his hand out to rub her back, chuckling when she hides her face in Sam’s neck shyly. 

“Someone was worried you were going to think she was stupid.” Sam says in a light tone of voice, wanting to keep (Y/N) happy, and not upset. “Even though I kept reassuring her you wouldn’t, she wanted to hear it directly from you. I thought we could come out here and you could see her for a few minutes while I make her a bottle.” 

Dean nods his head in understanding, outstretching his arms to her. She slowly lets go of Sam and lets Dean take her, him holding her in a different way. Instead of settling her on his hip, she’s instead right in front of him with her legs on either side of his waist, his arms clasped together under her bum. “Now, how could I think someone as cute as you is stupid, hmm?” He asks in a cooing tone, one not unlike Sam’s. “You’re absolutely adorable. I think it’s great that you can find a way to relax, okay? Whatever it is. I’m here for whatever you need, just like Sammy. Promise. I absolutely do not think you’re stupid.” 

(Y/N) blushes softly, nodding as she rests her head on Dean’s shoulder. A few minutes later, Sam is back with a warmed up bottle of milk, after having made sure that it wasn’t too warm. “Alright, sweetheart. Let’s get you this bottle and get you settled into bed, hmm?” 

She nods her head, opening her arms for Sam to take her again. Sam hands Dean the bottle quickly, so they trade for a moment until Sam gets (Y/N) settled comfortably in his arms once again. “Thanks, man.” He says quietly, and Dean knows he’s thanking him for more than just handing him the bottle. “We’re going to head to bed now. We’ll see you in the morning, and perhaps someone will still be little.” 

Dean nods his head when Sam thanks him, then grins softly. “I look forward to it.”


End file.
